Cara
by OldBillyBob
Copyright© 2020 by OldBillyBob
True Sex Story: A face from Andy's past brings back a flood of memories.
Caution: This True Sex Story contains strong sexual content, including Ma/Fa Consensual Romantic Heterosexual True Story Cheating .
“Find out who viewed your profile,” the email said. This was for my LinkedIn profile, which had to mean that someone was really bored. They’d have to be bored if they looked up Andy Curtis. I’m a retired property manager and have very few professional contacts these days. I keep thinking I should delete my account, but I never get around to it. I get maybe one view every few months and it’s usually someone like a financial planner trolling for potential clients. I figured what the heck and looked to see who had been checking me out. One person. That’s it. Her name was Cara Jackson Weaver. I had known someone named Cara, years ago, but the surname Weaver meant nothing to me. It only took one glance at her profile picture to tell me exactly who she was. It was the Cara I remembered! I thought back to the last time I had seen that face. It had been almost twenty-five years.
Of course, I checked her profile. All I really discovered was where she lived and where she worked but it seemed like she was doing pretty well for a woman who had been a stay-at-home mom in a shitty marriage when I met her.
(This is where the video goes blurry and the soundtrack plays eerie music as the flashback begins.)
Work was boring, except when it wasn’t, so I spent a fair amount of time in AOL chat rooms between the exciting parts. I had recently become a denizen of a room full of folks from our mid-sized city and had fun trading quips and jokes with a bunch of regulars. I had even been to a meet-up lunch attended by about a dozen of them.
One day, a newcomer had popped in under the chat name ShortGrl. In the conversation that followed her appearance, she mentioned going to a gym where I was a member and I commented that I worked out there so maybe I’d see her sometime. That got me a private message, in which we traded our real names along with descriptions of ourselves and a window of time where we might both be working out at the same time. I mentioned that I was going the next day and ShortGrl said she was going as well, so we coordinated our schedules. The next morning, I was on a treadmill and keeping an eye out for a 35-year-old woman, five-foot-one with short brown hair. I had been looking in the wrong direction, apparently, and didn’t spot her until she was starting up the treadmill next to me.
“Hi,” she said hesitantly as she got the machine running. “I’m Cara Roper.”
“I’m Andy Curtis,” I replied. “Were you looking for me?”
Her bright smile almost melted me. “Nice to meet you, HndyAndy,” she beamed. “I’m ShortGrl.”
Yes, HndyAndy was my chatroom name. Back then I was 45 and running a trim 170 pounds on my six-foot frame. Blue eyes and dark brown hair completed the picture. Maybe a little skinny, maybe a little geeky with the glasses I wore, but I think I looked OK.
I thought Cara was gorgeous, even in gym wear. At five-foot-one, she probably weighed about 110, which gave her legs some extra curvature that looked really nice in shorts. She was wearing a baggy t-shirt and loose-fitting shorts, so I couldn’t tell how the rest of her body was shaped. It didn’t much matter anyway. We were both married. I don’t know about Cara, but the only reason I agreed to meet her at all was the same reason I had for hanging around in the chatroom and going to lunch with its denizens: I was starved for human companionship. My wife was a workaholic who never had time for me, my son was off to college and my work only put me in contact with a dozen people in the course of a week.
Cara and I chatted a little as we walked on our treadmills. I found out she was married to a mid-level executive of the local branch of a big utility company. They had been married fifteen years and had one daughter, a thirteen-year-old named Shellee, who had just started eighth grade. She learned that I was 45, managed a complex of apartments here in town, had been married to my wife the lawyer for twenty years and that our son was out of state in his first year of college.
Not much happened that first day, other than our gym time and a nice conversation. Cara and I knocked off about the same time to head for our respective showers and I didn’t see her afterward. We had both promised to be back at the same time the next day, but that was it. In fact, that was all that happened for several weeks. We would show up at the gym around the same time, chat a little when we could, head off to the showers and that would be it.
One day, though, I came out of the locker room after my shower and Cara was at the snack bar near the entry door, buying herself a bottle of juice. I decided an OJ was a good idea and stood behind her at the counter, admiring her cute butt in her ‘mom jeans’ as she paid for her drink. She gave me a shy smile as she passed me and went to stand by the door.
When I had my own juice, I walked toward her. She looked around nervously, as if she expected someone to be watching, and motioned me ahead of her toward the parking lot. As I held the door for her to pass through, she said, “Tell me where you work. I want to stop by and talk.”
“Wood Lakes Apartments on Welborn Avenue,” I replied.
“See you in a half hour,” she replied and walked on.
Once we were out the door, Cara acted like she didn’t know me at all. It just felt odd. I saw her get into her car, a fairly new Nissan sedan, and start it up. I continued on to the old pickup that I drove and went on to work. I had a nicer car of my own, but the truck was one of the ‘perks’ of working where I did. Being the apartment complex manager also meant being the plumber, carpenter, electrician and all-around handyman. That was the story behind the screen name HndyAndy. The truck was perfect for hauling stuff. I was driving it that day because I had to pick up an order from the lumberyard. They had it ready for me, so I wasn’t delayed getting to my office after I picked it up.
True to her word, Cara came into my office thirty minutes after we had parted at the gym. “I can’t stay long,” she told me as she came in. “John will be checking up on me, and I should be at home when he calls.”
“O ... K...” I said. Obviously, this woman had something going on in her life, but it wasn’t my place to pry.
“He’s a little ... controlling,” Cara explained. “He gets jealous if he sees me talking to someone, men especially. If I don’t answer when he calls, I’ll have to tell him what I did and where I’ve been every minute of the day. Sometimes, he’ll leave the office and drive around looking for my car.”
“Really?” The man had to be totally insane.
“Yeah,” she sighed. “He’s wound pretty tight.”
“Does he hit you?” I asked.
“No,” she assured me. “There’s just a lot of questions all the time and he can get pretty loud about it.”
“Hmm.” I didn’t know what to say or do about any of that information.
“Don’t worry about it. I just wanted you to know what’s what,” she shrugged. “What’s your story?”
“My wife is a workaholic and my job is kind of isolated at times,” I told her. “I go online just to have people to talk to.”
“Works for me,” Cara grinned. “Everyone in the chatroom seems to like you, and my impression of you from the gym is that you’re an OK guy. I’d love to be someone you like to talk to.”
“That’d be fantastic,” I said with a smile. “Just drop by here whenever the mood strikes you. I’m usually around here. Want my phone number?”
“No!” she almost shouted. Regaining control, she added, “John snoops in my purse, goes through my cellphone contacts, checks the caller ID on the home phone. He’s convinced that I’m fooling around on him.”
“That’s just nuts.”
“You’re right about that,” she said. “The computer is safer, I think. If I see you on line, we can chat in IM. I figured out how to delete the chat logs so John won’t see them. If I can get away from the house, I’ll let you know if I can come over and see you.”
“Cool,” I nodded. “I can let you park your car in the garage behind the office. I usually park my personal car in it and drive the complex’s pickup for errands.”
“Fantastic,” she beamed. “The last thing I need is to get you involved in a fight with him when all we’re doing is talking. Anyway, I have to run for now.” She slipped out the door and was gone.
Cara dropped by my office about once a week for the next month or so and I learned more of her story. She told me that she and John were constantly on edge with each other because of his suspicious, jealous and controlling nature. I don’t know how she lived with that, other than that she was trying to keep her home life stable for their daughter, Shellee, who was thirteen when I first met Cara.
The only public place we really had much contact was at the gym, where we would try to get a machine next to each other if we could, and we would chat much like many folks would in that kind of setting. Otherwise, Cara and I did our best to appear as if we didn’t know each other in public. We weren’t actually supposed to know each other, after all.
One day, though, I was just about to step onto a treadmill next to hers and she gave me a nasty look and almost imperceptibly shook her head. At first, I didn’t know why she was suddenly so cold toward me and it almost hurt my feelings. It sank in later that she was warning me away for good reason. I moved to a machine a couple of rows behind her and watched as a man started up the machine that I had first aimed for. We chatted on line that afternoon and she told me the man was her husband. My first impression of him wasn’t good. He was decent-looking and in good physical shape. He had all his hair. That was all OK, but his eyes just looked cruel.
I would, of course, run into them in town occasionally. From what I could see, Shellee seemed to be a normal teen. She was a younger copy of her mom, short and slim with big brown eyes and a cute smile. John, as you might have gathered, was always watching what Cara did, his cruel eyes narrowing anytime she spoke to anyone. They narrowed even more whenever she spoke to a man. I did my best to remain a stranger in crowd whenever I saw them. I really was beginning to dislike this man.
I was also beginning to fall in love with Cara and looked forward to spending time with her, though I did my best not to start anything. Despite the loneliness my wife’s workaholic ways caused, things were actually good between us and I didn’t want to throw away twenty good years just to have a fling. I kept my distance from Cara, but that doesn’t mean I didn’t have my fantasies.
It was Cara who started things by kissing me one morning when it was time for her to leave my office. Not a friendly kiss on the cheek, either, but a full-blown, passionate, tongue-dueling kiss that had me instantly hard. She ground her tummy against my erection and giggled, kissing me once more.
“Hold that thought,” she smiled. “I’ll talk to you later on line.” She grabbed her purse and was out the door.
When she was gone, I put the closed sign on the office door and went into the bathroom to masturbate as I thought about the kiss and what it implied. Add in the fantasies I’d already been having about her and it wasn’t long before I was using toilet paper to mop up the mess I’d made. It was enough to take the immediate edge off but I was preoccupied as I unlocked the office and went back to my work.
I chatted with Cara on line a couple of hours later. Both of us admitted that we masturbated because of the kiss. She had me ready to jerk off again as she described how she’d used one of her vibrators to get herself off as she thought about having sex with me. Cara told me that she had been having thoughts about bedding me for a couple of weeks and had decided to go ahead and act on her desires. I realized I had fallen in love with her and was doing my best to keep my fantasies in check, but her kiss had destroyed my self-control. I had to let her know I felt the same.
“I want you,” I typed.
There was a long pause. I wasn’t sure what to expect when she didn’t answer for so long. Had I offended her? Was she getting cold feet?
“Wednesday morning after our workouts?” the answer came back.
“I have an empty furnished apartment here in the complex,” I answered. “See you Wednesday.”
We concluded our chat soon after that and I was in a daze the rest of the day. The next few days weren’t any better, since it was Friday when we put our plan in motion and wouldn’t see each other over the weekend. When Monday came, we met at the gym as usual, chatting cordially like near strangers while we sweated on adjacent treadmills. Cara was usually gone when I came out of the locker room and only stopped by the office once, on Monday, to talk. We ended up on the couch and she was in my lap with her arms around my neck as we made out like teenagers. Fortunately, I had put my ‘out of office’ sign up on the door.
“I can’t wait for Wednesday,” she panted between kisses. “Make sure you have some condoms, OK?”
I nodded, making a mental note to stop and get some. Our kissing finally halted when her cell phone rang. It was John, checking on her.
“I stopped by the drugstore for some makeup,” she lied. “I’ll be home in a few minutes.”
Turning to me, she sighed and said it was time for her to go. “He’ll be out in his car looking for me if I don’t go now.”
“Gym tomorrow?” I asked as she straightened her clothes.
“Sure thing,” she nodded, “and then here after the gym on Wednesday.”
It turns out that I didn’t go buy any condoms. I didn’t have to. That afternoon, Olga, the sassy grandmotherly Latina woman who cleaned vacated apartments for me, came into the office with a big box of them she found when she was cleaning out one of the apartments. It was mostly full, leaving maybe twenty of the two dozen the package originally held. I’m pretty sure she gave them to me as a joke.
“You never know when some pretty little thing will want to make a deal with you for the rent,” she teased. “You should keep these around.”
I dropped them in the trash, telling her she should know me better than that. The minute she left the building, though, they were moved to a drawer in my desk. Their sudden appearance had to be a sign.
The rest of the day was interminable, as was Tuesday. It was made worse when Cara didn’t come to the gym. She apologized later when we chatted on line. Shellee had been sick enough to stay home from school but Cara assured me that she’d be well enough to go back to school the next day, so our Wednesday plan was on. Since Shellee was napping, our chat turned into a conversation about what things we liked and disliked, sexually. For my part, I told her I was a big fan of cunnilingus. I could eat pussy all day if I had the chance. Cara said she’d give me a chance. What she wanted most was for wanted sex to be tender. I guess her husband wasn’t much on that, which fit with the rest of my observations about him.
We were both at the gym on Wednesday morning, but couldn’t get machines side-by-side. I was frustrated by not getting to chat with her and I could see the same frustration in her eyes. This was one of the days that she waited around and got herself an orange juice from the snack bar. Just like that first time, I stood behind her and admired her figure as we waited in line to buy our drinks. She was wearing a sundress. The hem of it was just above her knees and it had a modest scoop neckline and short sleeves. I thought it was a really sexy look on her but maybe I was thinking forward to what was going to happen later in the morning. She had, again, waited by the door while I bought my drink, letting me open the door for her and telling me she’d see me at my office very soon. Then she was out the door without leaving any clue that we knew each other.
I was a nervous mess when I got to my office. I parked my car out in front, leaving the garage open for Cara to park in, and was seated at my desk, nervously waiting when she came in. I somehow hadn’t noticed before that she was braless under her sundress, her small breasts barely wiggled beneath the material but her dark nipples were hard easily visible points that drew my eye.
“Let me get the key for that apartment,” I said, “and something else.”
The key was in my top desk drawer and the box of condoms was in the bottom drawer. Cara smiled when she saw me take out a strip of three and put them in my pocket.
“Lead the way,” she smiled.
I led her out of the office and down the walk to the apartment in question. To any outside observer, she appeared to be just another prospective tenant taking a tour of an apartment. That changed the moment we were in the apartment with the door closed behind us. Cara was the aggressor, pushing me back against the door and pulling my head down so we could kiss. I returned the kiss, wrapping my arms around her and dropping my hands to her round butt so I could squeeze the firm globes. We didn’t stay in the entryway very long. Cara was impatient and took my hand to lead me back to one of the bedrooms.
“You said you like to eat pussy,” she whispered after another kiss. “Would you like to eat mine? Right now?”
I grinned and nodded at her like a little boy who’s just been asked if he’d like ice cream. She smiled and lifted the hem of her sundress up to her waist. That’s when I found out she had no panties on. Her bush was close-cropped and trimmed into a neat triangle on her mound. Her dark pussy lips barely showed, but I could see moisture already gathering in the slit between them. She finished pulling the dress off and laid it carefully on a bedside chair before she lay back on the bed with her legs spread wide. I wasted no time in going down on her. I truly love to eat pussy. It was one of the things I missed most as my wife and I found our passion dying.
Cara was so delicious I tried to make up for the lack of pussy in my diet in one helping. Nothing else existed for a little while except my mouth and Cara’s juicy slit. She had at least three orgasms before she pushed my face away. “God!” she panted. “I haven’t ever had my pussy devoured like that, and certainly not in the past ten years. Now, trade me places and let me suck you off.” I dutifully dropped my pants and boxers and sat with my ass on the edge of the bed. Cara gave a great blowjob, and greedily swallowed every drop I gave her – and I gave it to her much too quickly. She kept sucking until she had coaxed me back to hardness.
Licking her lips as she rose up from her knees, Cara turned and rifled through my pants pockets to find the strip of condoms I’d grabbed from my desk. She tore one from the strip of three and laid the other two on the bedside table before she tore open the foil packet, retrieved the contents and rolled the rubber sheath down my eager erection.
With protection in place, Cara straddled me, gently guiding my hard-on to her opening. She was wet enough to slide down its full length in one easy motion. I had been watching my dick disappear into her folds but her sigh drew my attention to her face. Her eyes were half-closed and her expression could only be described as blissful. She was off in another world for the time being. It gave me a chance to study her body, since this was the first time I’d ever seen her naked.
I employed my hands as part of the study, softly trailing my fingers over her skin while I gazed at her beautiful features. Even though Cara was only five-one, her build made her look long and lean. In keeping with that, she had a gracefully long neck and slender arms. Her breasts were just little cones, capped with chocolate-colored areolas just bigger than quarters and eraser-sized nipples. I couldn’t resist cupping them in my hands and gently pinching the nipples between my thumb and forefinger.
“I wish they were bigger,” she sighed.
“I’ve always loved little tits,” I answered. This was true, my wife’s breasts were only a B cup, “and these are about the sweetest little titties I’ve ever seen or felt.”
She leaned down to kiss me as thanks for the comment, giving me an opportunity to run my hands up and down her smooth back, feeling the fine muscles as she moved and flexed on top of me. I also grasped the firm globes of her ass, kneading the muscular cheeks as I pushed myself up into her. The kiss broke off and she sat up straight again, closing her eyes and rocking slowly as we made love.
My eyes and hands continued their tour, settling on her slightly rounded tummy with its slight stretch marks, the unavoidable consequence of motherhood, and the C-section scar that ran vertically from just below her belly button almost to her curly pubic hair.
“I know it’s ugly,” she apologized, “having Shellee almost killed me. It was an emergency surgery because we were both in danger. I had my tubes tied because I couldn’t risk another pregnancy.”
I quieted her by gently putting a finger on her lips. “Actually, I think it’s beautiful,” I said as a finger from my other hand traced its way down the pink line. “It’s a visible reminder of the love you have for your daughter. A battle scar worthy of a warrior.”
Cara looked down at me with a kind of adoration I’ve never seen before. Then she started to cry and collapsed on top of me, sobbing into my shoulder. I was afraid my hard-on would wilt as she drenched my shoulder and neck with tears, but the wracking sobs that shook her also caused some interesting things to go on in her pussy, so my cock stayed interested while I tried to calm my suddenly emotional partner. All I could think of to do was hold her gently and stroke her back.
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